Tom Smykowski is a seasoned Technical Due Diligence Engineer based in Poland, offering remote staff-level expertise to EU, UK, and US-based teams. With nearly two decades of product delivery experience spanning engineering, UX, and product thinking, Tom provides the critical technical assessment founders, investors, and CTOs need during acquisitions, investments, or major modernization projects. He combines hands-on code review with strategic architecture evaluation, focusing on scalability, security, maintainability, and technical debt to deliver actionable, risk-mitigating insights.
What is Technical Due Diligence in Software Engineering?
Technical due diligence is a systematic evaluation of a software company's technology assets, codebase, architecture, and engineering practices. It's a critical process undertaken during mergers, acquisitions, venture capital investments, or major partnership agreements. The goal is to uncover hidden risks, validate claimed capabilities, assess technical debt, and evaluate the long-term viability and scalability of the product's technology foundation.
For investors and acquiring companies, it answers fundamental questions: Is the technology sound and secure? Can it scale to meet growth projections? What is the true state of the codebase and the team behind it? A thorough technical audit examines everything from infrastructure and data architecture to development workflows and team competency. As a Technical Due Diligence Engineer, Tom translates complex technical realities into clear, business-focused reports that inform critical financial and strategic decisions.
This process goes far beyond a superficial glance at a tech stack. It involves deep-dive code analysis, architecture diagramming, interviews with key technical personnel, and assessment of operational metrics like deployment frequency, incident response, and security posture. The output is a comprehensive risk profile and a roadmap for post-transaction integration or necessary remediation, ensuring stakeholders proceed with eyes wide open.
Key Areas of Assessment in a Technical Audit
A comprehensive technical due diligence review covers several core pillars. First is Code Quality and Architecture. Tom examines the codebase for adherence to modern best practices, modularity, test coverage, and documentation. He assesses whether the architecture is monolithic or microservices-based, evaluates API design, and checks for tight coupling or unsustainable dependencies. His experience with large-scale systems at companies like Printify, where he worked on a design system for a platform serving 10M+ merchants, provides a keen eye for scalable, maintainable structure.
The second pillar is Infrastructure, Security, and Compliance. This involves reviewing hosting providers, deployment pipelines, disaster recovery plans, and data governance. Security audits check for common vulnerabilities, access control models, and data encryption standards. For companies in regulated industries or those handling sensitive data, compliance with standards like GDPR, SOC 2, or HIPAA is scrutinized. Tom's background includes work on compliance-focused features at Croissant, a workplace platform, giving him practical insight into building secure, auditable systems.
Finally, the assessment covers Team and Processes. The competency of the engineering team, the effectiveness of their Agile or DevOps practices, and the health of their CI/CD pipeline are evaluated. Tom reviews tools for project management, monitoring, and collaboration. He also assesses technical leadership and knowledge-sharing practices, drawing on his own extensive experience in mentoring, technical writing, and public speaking. A strong team with robust processes is often a more valuable asset than the code itself.
The Due Diligence Process: From Scoping to Reporting
Tom's engagement as a Technical Due Diligence Engineer follows a structured, transparent process designed to deliver maximum insight with minimal disruption. It begins with a Scoping and Planning Phase. He collaborates with the client to understand the specific goals of the diligence, the timeline, and any particular areas of concern. Key documents like architecture diagrams, recent audit reports, and organizational charts are requested. Access to code repositories, staging environments, and key team members is arranged, often under strict NDAs and confidentiality agreements.
The core of the work is the Investigation and Analysis Phase. This is a period of intense, focused review. Tom conducts automated and manual code reviews, analyzes database schemas and query patterns, tests API endpoints, and evaluates infrastructure configuration. He holds confidential interviews with lead developers, DevOps engineers, and the CTO to understand system rationale and team dynamics. He also examines operational metrics related to system performance, uptime, and deployment frequency. His remote setup from Poland allows him to work effectively across EU, UK, and US time zones, scheduling interviews during convenient overlaps.
The engagement culminates in the Reporting and Advisory Phase. Tom synthesizes his findings into a clear, prioritized report. This is not merely a list of bugs; it's a strategic document that categorizes findings by severity (critical, high, medium, low), estimates remediation effort, and provides actionable recommendations. The report highlights deal-breakers, quantifies technical debt, and outlines a post-acquisition integration or modernization plan. He then presents the findings to stakeholders, answering questions and helping them understand the implications for valuation, negotiation, and future technology strategy.
Leveraging AI and Modern Tooling in Due Diligence
Modern technical due diligence leverages advanced tooling and AI to enhance depth and accuracy. Tom incorporates AI-assisted code analysis tools to rapidly scan large codebases for patterns, anti-patterns, security vulnerabilities, and code duplication. These tools can provide a quantitative baseline for code quality, which is then enriched by human expertise. His consulting offerings include AI Software Factory setup, demonstrating his proficiency in integrating AI agents into development and audit workflows to increase efficiency and coverage.
Beyond code, infrastructure-as-code (IaC) analysis and dependency scanning are critical. Tools are used to audit cloud configuration for security missteps, review container definitions, and analyze software bill of materials (SBOM) for licensing risks and known vulnerabilities in third-party libraries. Tom's full-stack experience with technologies like Vue.js, TypeScript, Supabase, and AG Grid means he can effectively evaluate both frontend and backend dependencies, understanding their impact on performance and maintainability.
The human element remains irreplaceable. Tooling provides data, but interpretation and context come from experience. Tom's background as a founder of Websoul, which served over 32,000 businesses, and his work with industrial SaaS at Fream give him a unique perspective. He can discern whether a piece of technical debt is a minor nuisance or a fundamental architectural flaw that will cripple scaling. This blend of automated insight and seasoned judgment is what delivers a truly valuable due diligence assessment.
Case Studies and Relevant Experience
Tom's career provides a strong foundation for technical due diligence across various domains. His role as a Staff Software Engineer at Croissant involved deep work on a platform requiring high compliance and collaboration standards. This experience is directly applicable to auditing SaaS products that must adhere to strict regulatory requirements, assessing how compliance is baked into the architecture and development lifecycle.
At Printify, Tom contributed to a major design system rebrand ahead of a merger, working within a frontend team of around 60 engineers. This exposure to a large, complex codebase serving millions of users is ideal for evaluating scaling challenges and codebase cohesion in high-growth companies. Understanding how a design system governs UI consistency and developer efficiency is a key due diligence checkpoint for product-centric companies.
His experience as the founder of Websoul offers invaluable insight into startup technology. Building a marketing automation platform to serve tens of thousands of businesses required making pragmatic technology choices, managing technical debt, and scaling infrastructure. This founder-level perspective allows him to empathetically yet critically assess other startups, understanding the trade-offs they've likely made and identifying which ones pose existential risks versus being manageable shortcuts.
When This is a Good Fit
Engaging Tom as your Technical Due Diligence Engineer is an ideal fit if you are a venture capital firm, private equity investor, or a company considering an acquisition or major partnership and need an independent, expert assessment of a target's technology. It's also highly suitable for founders or CTOs preparing for a funding round who want to proactively identify and remediate technical risks before investor diligence begins. If you require a staff-level engineer who can work remotely from Poland with seamless communication across EU, UK, and US time zones, and who delivers clear, business-aligned technical analysis, then this collaboration will provide the clarity and confidence needed for your critical decisions.